Search and Rent Legacy Trail Condos

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Legacy Trail condo rentals

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1176)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$167 nightly
The price is $187
Dec 23 - Dec 24
Total with taxes and fees
Captiva Beach Resort

Condo in Port Charlotte

2/2 Spacious Unit
9.2 out of 10, Wonderful, (10)
"Great location close to everything.beautiful place well stocked nice host."
United States
Elisabeth B.
$256 nightly
The price is $283
Dec 23 - Dec 24
Total with taxes and fees
2/2 Spacious Unit

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
$546 nightly
The price is $587
Jan 4 - Jan 5, 2026
Total with taxes and fees
Chadwick Cove Resort & Marina

Condo in Holmes Beach

Alamanda Villas
3.5 star property
10.0 out of 10, Exceptional, (3)
"The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay."
United States
Traci
$407 nightly
The price is $438
Dec 23 - Dec 24
Total with taxes and fees
Alamanda Villas

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (577)
"Great location, recent updates"
United States
Michael
$184 nightly
The price is $208
Jan 7 - Jan 8, 2026
Total with taxes and fees
A Beach Retreat
10.0 out of 10, Exceptional, (119)
"We enjoyed our stay. Host is nice and respond quickly. "
Canada
Sonia S.
$301 nightly
The price is $336
Jan 3 - Jan 4, 2026
Total with taxes and fees
Lovely Waterfront Condo: Two Pools~Private Lanai~Fast WiFi! Near IMG~AMI~Beaches

Condo in Longboat Key

Sunset and Beach view unit 402
9.8 out of 10, Exceptional, (14)
"Loved our stay. Margaret at the front desk was amazing. Hope to come back again soon. "
United States
slimetastic !.
$330 nightly
The price is $363
Dec 23 - Dec 24
Total with taxes and fees
Sunset and Beach view unit 402
9.8 out of 10, Exceptional, (60)
"It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. "
United States
Marge G.
$339 nightly
The price is $379
Jan 17 - Jan 18, 2026
Total with taxes and fees
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Condo in Bayou Oaks

Riverside Oasis 1Bed/1Bath
9.2 out of 10, Wonderful, (40)
"Excellent place to stay"
United States
garry s.
$125 nightly
The price is $139
Jan 4 - Jan 5, 2026
Total with taxes and fees
Riverside Oasis 1Bed/1Bath
9.8 out of 10, Exceptional, (39)
"Perfect for 2 adults and 2 kids. The house was very clean and all the extras in the kitchen were nice. Also, beach essentials are onsite so no need to bring much. Found lots of sharks teeth too! "
United States
Koren L.
$321 nightly
The price is $357
Jan 14 - Jan 15, 2026
Total with taxes and fees
Steps to Water! Sea Glass - Beach to Bay, Heated Pool and Dock
9.4 out of 10, Exceptional, (29)
"The condo itself had everything we needed the covered out door balcony was perfect for relaxing with a drink before dinner with out having to be concerned with the sun or rain "
Canada
Joseph D C.
$519 nightly
The price is $581
Jan 3 - Jan 4, 2026
Total with taxes and fees
Newly Renovated Jamaica Royale Unit, Heated Pools
9.8 out of 10, Exceptional, (148)
"Great location, clean, everything we needed for a low key beach vacation!"
United States
Stephanie H.
$260 nightly
The price is $290
Dec 29 - Dec 30
Total with taxes and fees
Beautiful 2BR Condo: Heated Pools~Fast WiFi. Near IMG~Beaches~AMI~Restaurants.
9.8 out of 10, Exceptional, (114)
"Enjoyed our stay, we will return for future fun in AMI"
United States
Karen J.
$319 nightly
The price is $355
Jan 7 - Jan 8, 2026
Total with taxes and fees
Superb Waterfront Condo: Heated Pools~Lanai~WiFi! By IMG~AMI~Beaches~Restaurants
8.8 out of 10, Excellent, (42)
"Enjoyed our stay"
United States
Susan C.
$306 nightly
The price is $341
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Condo in Bradenton

Beautifully furnished condo
9.8 out of 10, Exceptional, (148)
"Beautiful property and quiet. "
United States
Sandy K.
$262 nightly
The price is $292
Jan 5 - Jan 6, 2026
Total with taxes and fees
Beautifully furnished condo
9.8 out of 10, Exceptional, (91)
"Excellent condo. Very clean and well equipped."
United Kingdom
john l.
Shorewalk Sunny Bella Rosa • 2BR Villa • 2 Pools & Hot Tubs • Near IMG / Beaches
9.6 out of 10, Exceptional, (21)
"Cool place. Everything just as mentioned. Kids had a blast at pool and place was super clean"
United States
Jason G.
$356 nightly
The price is $392
Dec 23 - Dec 24
Total with taxes and fees
*Charming 2bed 2 bath 6 mins from IMG*
9.8 out of 10, Exceptional, (101)
"Great location and the private beach was so nice! "
United States
Ashley N.
$353 nightly
The price is $395
Jan 4 - Jan 5, 2026
Total with taxes and fees
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
9.4 out of 10, Exceptional, (12)
"Enjoyed our stay in this quiet little place with close access to restaurants and just a few minutes from Bradenton. Would come back!"
United States
Todd B.
$406 nightly
The price is $453
Dec 23 - Dec 24
Total with taxes and fees
Charming Longboat Key Bungalow with beach access minutes away…
9.6 out of 10, Exceptional, (21)
"Nice location, clean"
United States
Al H.
Bayfront Condo Walkable to Everything. Unit 3
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

Legacy Trail Condo Rentals information

Number of reviews
2,731
Accommodation
420 Condo Rentals
Lowest Price
$139
Highest Price
$587

Explore a world of travel with Expedia